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The crystal structure of the title compound, C13H16N2O4, (1), reveals that the molecule exists in the solid state in the equatorial conformation. Thus, the through-bond interaction present in the axial conformation is not strong enough to overcome the syn–diaxial interactions between the axial methyl substituent and the axial H atoms on each of the ring C atoms β to N. The C—OPNB (PNB is p-nitrobenzoate) bond distance is 1.4630 (16) Å, which is not significantly different from the corresponding C—OPNB distance in 4-tert-butylcyclohexyl 4-nitrobenzoate. The structure of (1) was determined at 130 K.
Supporting information
CCDC reference: 203012
Key indicators
- Single-crystal X-ray study
- T = 130 K
- Mean (C-C) = 0.002 Å
- R factor = 0.041
- wR factor = 0.097
- Data-to-parameter ratio = 11.8
checkCIF results
No syntax errors found
ADDSYM reports no extra symmetry
Alert Level C:
REFLT_03
From the CIF: _diffrn_reflns_theta_max 27.50
From the CIF: _reflns_number_total 2787
TEST2: Reflns within _diffrn_reflns_theta_max
Count of symmetry unique reflns 3044
Completeness (_total/calc) 91.56%
Alert C: < 95% complete
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
1 Alert Level C = Please check
Data collection: SMART (Bruker, 2000); cell refinement: SMART; data reduction: SAINT (Bruker, 1999); program(s) used to solve structure: SHELXTL (Bruker, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.
Crystal data top
C13H16N2O4 | Z = 2 |
Mr = 264.28 | F(000) = 280 |
Triclinic, P1 | Dx = 1.321 Mg m−3 |
Hall symbol: -P 1 | Melting point: 93 K |
a = 6.3348 (8) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 7.697 (1) Å | Cell parameters from 1094 reflections |
c = 13.9423 (18) Å | θ = 2.7–27.5° |
α = 99.030 (2)° | µ = 0.10 mm−1 |
β = 92.142 (2)° | T = 130 K |
γ = 97.528 (3)° | Plate, colourless |
V = 664.43 (15) Å3 | 0.50 × 0.30 × 0.07 mm |
Data collection top
Bruker CCD area-detector diffractometer | 1915 reflections with I > 2σ(I) |
Radiation source: sealed tube | Rint = 0.032 |
Graphite monochromator | θmax = 27.5°, θmin = 1.5° |
φ and ω scans | h = −8→4 |
3614 measured reflections | k = −9→8 |
2787 independent reflections | l = −17→16 |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.041 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.097 | All H-atom parameters refined |
S = 0.88 | w = 1/[σ2(Fo2) + (0.0462P)2] where P = (Fo2 + 2Fc2)/3 |
2787 reflections | (Δ/σ)max < 0.001 |
236 parameters | Δρmax = 0.20 e Å−3 |
0 restraints | Δρmin = −0.19 e Å−3 |
Special details top
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F2, conventional
R-factors R are based on F, with F set to zero for
negative F2. The threshold expression of F2 >
σ(F2) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F2 are statistically about twice as large
as those based on F, and R-factors based on ALL data will be
even larger. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
C1 | 0.2048 (2) | 0.3072 (2) | 0.66782 (10) | 0.0273 (3) | |
H1 | 0.260 (2) | 0.4324 (19) | 0.6786 (9) | 0.026 (4)* | |
C2 | 0.0202 (2) | 0.2667 (2) | 0.59229 (10) | 0.0288 (3) | |
H2A | −0.092 (2) | 0.3469 (19) | 0.6126 (10) | 0.034 (4)* | |
H2B | −0.041 (2) | 0.1428 (19) | 0.5912 (10) | 0.032 (4)* | |
C3 | 0.0987 (2) | 0.2894 (2) | 0.49284 (10) | 0.0305 (4) | |
H3A | −0.020 (2) | 0.2537 (18) | 0.4443 (10) | 0.032 (4)* | |
H3B | 0.151 (2) | 0.4145 (18) | 0.4930 (9) | 0.024 (4)* | |
C4 | 0.4462 (2) | 0.2273 (2) | 0.53698 (11) | 0.0299 (3) | |
H4A | 0.510 (2) | 0.3587 (19) | 0.5389 (10) | 0.035 (4)* | |
H4B | 0.558 (2) | 0.1508 (18) | 0.5155 (10) | 0.032 (4)* | |
C5 | 0.3794 (2) | 0.1974 (2) | 0.63776 (11) | 0.0312 (4) | |
H5A | 0.325 (2) | 0.069 (2) | 0.6370 (10) | 0.034 (4)* | |
H5B | 0.505 (2) | 0.2232 (19) | 0.6840 (10) | 0.037 (4)* | |
C6 | 0.3289 (3) | 0.1980 (2) | 0.36842 (12) | 0.0375 (4) | |
H6A | 0.207 (3) | 0.155 (2) | 0.3204 (12) | 0.052 (5)* | |
H6B | 0.443 (3) | 0.125 (2) | 0.3498 (11) | 0.047 (5)* | |
H6C | 0.383 (2) | 0.325 (2) | 0.3606 (11) | 0.049 (5)* | |
C7 | 0.2210 (2) | 0.33825 (19) | 0.84218 (10) | 0.0301 (3) | |
C8 | 0.1023 (2) | 0.28964 (18) | 0.92706 (10) | 0.0281 (3) | |
C9 | −0.1065 (2) | 0.2015 (2) | 0.91485 (11) | 0.0341 (4) | |
H9 | −0.175 (2) | 0.167 (2) | 0.8494 (11) | 0.041 (4)* | |
C10 | −0.2151 (2) | 0.1644 (2) | 0.99466 (11) | 0.0356 (4) | |
H10 | −0.355 (3) | 0.107 (2) | 0.9889 (12) | 0.053 (5)* | |
C11 | −0.1135 (2) | 0.21507 (19) | 1.08604 (10) | 0.0306 (3) | |
C12 | 0.0934 (2) | 0.3020 (2) | 1.10049 (11) | 0.0332 (4) | |
H12 | 0.157 (2) | 0.337 (2) | 1.1658 (11) | 0.045 (4)* | |
C13 | 0.2006 (2) | 0.3385 (2) | 1.02006 (11) | 0.0319 (4) | |
H13 | 0.335 (2) | 0.398 (2) | 1.0292 (10) | 0.038 (4)* | |
N1 | 0.26463 (17) | 0.17903 (15) | 0.46569 (8) | 0.0274 (3) | |
N2 | −0.2311 (2) | 0.17568 (18) | 1.17124 (9) | 0.0380 (3) | |
O1 | 0.11629 (14) | 0.26353 (13) | 0.75790 (7) | 0.0313 (3) | |
O2 | 0.38872 (15) | 0.43602 (14) | 0.84938 (7) | 0.0424 (3) | |
O3 | −0.40037 (18) | 0.07581 (17) | 1.15680 (8) | 0.0597 (4) | |
O4 | −0.15396 (17) | 0.24315 (16) | 1.25239 (7) | 0.0466 (3) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0263 (7) | 0.0277 (8) | 0.0269 (8) | −0.0008 (6) | 0.0029 (6) | 0.0046 (6) |
C2 | 0.0226 (7) | 0.0332 (9) | 0.0311 (8) | 0.0046 (7) | 0.0017 (6) | 0.0057 (7) |
C3 | 0.0266 (8) | 0.0363 (9) | 0.0297 (8) | 0.0062 (7) | 0.0011 (6) | 0.0079 (7) |
C4 | 0.0231 (7) | 0.0310 (9) | 0.0353 (9) | 0.0041 (7) | 0.0021 (6) | 0.0041 (7) |
C5 | 0.0259 (8) | 0.0367 (9) | 0.0309 (8) | 0.0044 (7) | −0.0027 (6) | 0.0061 (7) |
C6 | 0.0385 (9) | 0.0438 (11) | 0.0330 (9) | 0.0119 (8) | 0.0071 (7) | 0.0088 (8) |
C7 | 0.0275 (8) | 0.0317 (8) | 0.0289 (8) | −0.0004 (6) | −0.0019 (6) | 0.0032 (6) |
C8 | 0.0272 (7) | 0.0265 (8) | 0.0291 (8) | 0.0015 (6) | 0.0004 (6) | 0.0020 (6) |
C9 | 0.0329 (8) | 0.0388 (9) | 0.0268 (8) | −0.0051 (7) | −0.0022 (7) | 0.0025 (7) |
C10 | 0.0292 (8) | 0.0410 (9) | 0.0327 (9) | −0.0068 (7) | 0.0003 (7) | 0.0042 (7) |
C11 | 0.0323 (8) | 0.0322 (8) | 0.0269 (8) | 0.0028 (6) | 0.0041 (6) | 0.0046 (6) |
C12 | 0.0330 (8) | 0.0368 (9) | 0.0275 (8) | 0.0005 (7) | −0.0041 (7) | 0.0032 (7) |
C13 | 0.0249 (8) | 0.0349 (9) | 0.0328 (8) | −0.0027 (6) | −0.0018 (6) | 0.0030 (7) |
N1 | 0.0260 (6) | 0.0306 (7) | 0.0259 (6) | 0.0060 (5) | 0.0023 (5) | 0.0038 (5) |
N2 | 0.0382 (8) | 0.0441 (8) | 0.0303 (7) | 0.0004 (6) | 0.0026 (6) | 0.0061 (6) |
O1 | 0.0292 (5) | 0.0362 (6) | 0.0256 (5) | −0.0051 (4) | 0.0015 (4) | 0.0042 (4) |
O2 | 0.0334 (6) | 0.0542 (7) | 0.0330 (6) | −0.0143 (5) | −0.0002 (5) | 0.0037 (5) |
O3 | 0.0500 (8) | 0.0795 (10) | 0.0394 (7) | −0.0255 (7) | 0.0085 (6) | 0.0060 (6) |
O4 | 0.0445 (7) | 0.0666 (8) | 0.0262 (6) | 0.0024 (6) | −0.0003 (5) | 0.0046 (5) |
Geometric parameters (Å, º) top
C1—O1 | 1.4630 (16) | C6—H6B | 0.990 (16) |
C1—C2 | 1.5111 (18) | C6—H6C | 1.018 (17) |
C1—C5 | 1.510 (2) | C7—O2 | 1.2101 (16) |
C1—H1 | 0.968 (14) | C7—O1 | 1.3345 (15) |
C2—C3 | 1.518 (2) | C7—C8 | 1.496 (2) |
C2—H2A | 1.019 (15) | C8—C13 | 1.391 (2) |
C2—H2B | 0.980 (14) | C8—C9 | 1.3969 (19) |
C3—N1 | 1.4603 (18) | C9—C10 | 1.378 (2) |
C3—H3A | 0.973 (14) | C9—H9 | 0.978 (15) |
C3—H3B | 0.976 (13) | C10—C11 | 1.381 (2) |
C4—N1 | 1.4616 (17) | C10—H10 | 0.935 (16) |
C4—C5 | 1.525 (2) | C11—C12 | 1.3837 (19) |
C4—H4A | 1.034 (14) | C11—N2 | 1.4761 (18) |
C4—H4B | 1.004 (14) | C12—C13 | 1.380 (2) |
C5—H5A | 1.001 (15) | C12—H12 | 0.965 (15) |
C5—H5B | 0.982 (14) | C13—H13 | 0.906 (15) |
C6—N1 | 1.4540 (19) | N2—O4 | 1.2233 (15) |
C6—H6A | 0.990 (16) | N2—O3 | 1.2247 (15) |
| | | |
O1—C1—C2 | 105.68 (10) | H6A—C6—H6B | 107.1 (13) |
O1—C1—C5 | 111.02 (11) | N1—C6—H6C | 114.0 (9) |
C2—C1—C5 | 110.75 (13) | H6A—C6—H6C | 107.2 (12) |
O1—C1—H1 | 108.1 (8) | H6B—C6—H6C | 107.5 (13) |
C2—C1—H1 | 110.8 (8) | O2—C7—O1 | 124.42 (13) |
C5—C1—H1 | 110.4 (8) | O2—C7—C8 | 124.05 (13) |
C1—C2—C3 | 110.17 (12) | O1—C7—C8 | 111.52 (11) |
C1—C2—H2A | 109.1 (8) | C13—C8—C9 | 119.70 (14) |
C3—C2—H2A | 111.9 (8) | C13—C8—C7 | 118.99 (12) |
C1—C2—H2B | 107.0 (8) | C9—C8—C7 | 121.28 (12) |
C3—C2—H2B | 109.4 (8) | C10—C9—C8 | 120.10 (14) |
H2A—C2—H2B | 109.1 (12) | C10—C9—H9 | 120.3 (9) |
N1—C3—C2 | 111.64 (12) | C8—C9—H9 | 119.6 (9) |
N1—C3—H3A | 107.9 (8) | C9—C10—C11 | 118.84 (14) |
C2—C3—H3A | 109.1 (8) | C9—C10—H10 | 122.1 (10) |
N1—C3—H3B | 110.6 (8) | C11—C10—H10 | 119.0 (10) |
C2—C3—H3B | 109.2 (8) | C10—C11—C12 | 122.43 (14) |
H3A—C3—H3B | 108.3 (11) | C10—C11—N2 | 118.55 (13) |
N1—C4—C5 | 110.73 (11) | C12—C11—N2 | 119.02 (12) |
N1—C4—H4A | 110.0 (7) | C13—C12—C11 | 118.23 (13) |
C5—C4—H4A | 110.0 (8) | C13—C12—H12 | 122.4 (9) |
N1—C4—H4B | 107.8 (8) | C11—C12—H12 | 119.4 (9) |
C5—C4—H4B | 109.9 (8) | C12—C13—C8 | 120.70 (14) |
H4A—C4—H4B | 108.4 (11) | C12—C13—H13 | 118.6 (9) |
C1—C5—C4 | 109.53 (12) | C8—C13—H13 | 120.7 (9) |
C1—C5—H5A | 109.0 (8) | C6—N1—C3 | 110.08 (12) |
C4—C5—H5A | 110.3 (8) | C6—N1—C4 | 111.18 (12) |
C1—C5—H5B | 113.1 (9) | C3—N1—C4 | 109.89 (12) |
C4—C5—H5B | 109.8 (9) | O4—N2—O3 | 123.51 (13) |
H5A—C5—H5B | 105.1 (11) | O4—N2—C11 | 118.41 (12) |
N1—C6—H6A | 110.1 (9) | O3—N2—C11 | 118.08 (12) |
N1—C6—H6B | 110.7 (9) | C7—O1—C1 | 118.26 (10) |
| | | |
O1—C1—C2—C3 | −174.20 (12) | N2—C11—C12—C13 | −179.71 (14) |
C5—C1—C2—C3 | −53.88 (17) | C11—C12—C13—C8 | 0.3 (2) |
C1—C2—C3—N1 | 56.30 (17) | C9—C8—C13—C12 | −0.5 (2) |
O1—C1—C5—C4 | 172.16 (11) | C7—C8—C13—C12 | 177.51 (14) |
C2—C1—C5—C4 | 55.07 (16) | C2—C3—N1—C6 | 177.42 (13) |
N1—C4—C5—C1 | −58.72 (17) | C2—C3—N1—C4 | −59.80 (15) |
O2—C7—C8—C13 | −9.1 (2) | C5—C4—N1—C6 | −176.98 (13) |
O1—C7—C8—C13 | 172.31 (12) | C5—C4—N1—C3 | 60.89 (16) |
O2—C7—C8—C9 | 168.93 (14) | C10—C11—N2—O4 | −169.27 (14) |
O1—C7—C8—C9 | −9.7 (2) | C12—C11—N2—O4 | 10.3 (2) |
C13—C8—C9—C10 | 0.5 (2) | C10—C11—N2—O3 | 11.3 (2) |
C7—C8—C9—C10 | −177.46 (14) | C12—C11—N2—O3 | −169.09 (14) |
C8—C9—C10—C11 | −0.3 (2) | O2—C7—O1—C1 | −2.4 (2) |
C9—C10—C11—C12 | 0.1 (2) | C8—C7—O1—C1 | 176.18 (11) |
C9—C10—C11—N2 | 179.72 (14) | C2—C1—O1—C7 | −158.28 (12) |
C10—C11—C12—C13 | −0.1 (2) | C5—C1—O1—C7 | 81.57 (15) |
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